Winchester, VA Homes

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  /49

  $499,870

  • 5 Beds
  • 3 Baths
  • 3,116 Sq Ft

  110 Carter Place, Winchester, VA 22602

  Extensive Renovations: The home has been fully renovated in 2025, including updates to kitchen, bathrooms, flooring, and fresh paint throughout. Designed to accommodate two families comfortably, featuring large rooms that are flooded with natural light like the entire house. The lower level is equipped with wheelchair-accessible features, enhancing mobility and convenience. Ideal for

  Rodrigo Cruz Long & Foster Real Estate, Inc.

  110 Carter Place, Winchester, VA 22602
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  /20

  $1,431 - $1,650 per month

  Preston Place - Tax Credit

  2-3 Beds

  124 Castlebridge Ct, Winchester, VA 22602

  Preston Place Apartments and Townhomes are a remarkable blend of style and value. Almost everything is nearby, from schools to shopping, restaurants, parks and interstate highways. Conveniently located on Airport Drive one-half mile from the Winchester Regional Airport. Dulles Airport is also less than thirty minutes away. It’s hard to find a more convenient location.

  124 Castlebridge Ct, Winchester, VA 22602
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  /28

  $400,000 Sold Jun 06, 2025

  • 2,001 Sq Ft
  • $200/SF

  • 3 Beds
  • 2.5 Baths
  • Built 1920

  1203 Valley Ave, Winchester, VA 22601

  This cozy, 1920s farmhouse sits on a spacious corner lot a few blocks from Old Town. The sunny yellow façade pairs with an inviting covered porch spanning the front of the home—the ideal place for rocking chairs and other furniture. Inside, warm hues combine with real hardwood floors, plus custom trim details like classic, three-piece baseboard and custom stairway newel posts to bring out the

  Dan Whitacre Colony Realty

  1203 Valley Ave, Winchester, VA 22601
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  /36

  Est $480,387 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft

  1960 Siler Rd, Winchester, VA 22603

  1960 Siler Rd, Winchester, VA 22603
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  /25

  $475,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,092 Sq Ft

  1709 Reaves St, Winchester, VA 22601

  Please take off shoes and give feedback. Step into this beautifully cared-for home featuring new roof (2023) New HVAC System (2024) new LVP floors throughout the basement a spacious, inviting layout. The large kitchen offers plenty of room for meal prep and flows effortlessly into the dining and living rooms — perfect for family gatherings and entertaining. The finished basement boasts a

  Alexandra Brown Berkshire Hathaway HomeServices PenFed Realty

  1709 Reaves St, Winchester, VA 22601
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  /17

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Condo for Rent

  136 4 Brookland Ct Unit 4, Winchester, VA 22602

  Welcome to this sun-drenched, updated 2 bedroom 2 bathroom condo located in the desirable Park Place community! This newly remodeled home with convenient first floor access has been freshly painted and features brand new LVP flooring and a stunning kitchen. The modern kitchen is a true standout, featuring new elegant cabinetry, sleek granite countertops, and all new stainless steel appliances.

  Joelle Graham Weichert, REALTORS

  136 4 Brookland Ct Unit 4, Winchester, VA 22602
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  /70

  $585,000 Sold Jun 06, 2025

  • 3,078 Sq Ft
  • $190/SF
  • 0 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2004

  104 Quigley Ct, Winchester, VA 22602

  Imagine Summer Days in your own Private Paradise, Living in this Gorgeous Colonial with a Backyard Oasis!Nestled at the end of a peaceful cul-de-sac, this beautifully maintained 4-bedroom, 2.5-bath colonial offers the perfect blend of elegance, comfort, and outdoor living. The crown jewel of this home is the stunning inground saltwater pool, complete with a gas heater replaced in 2019, a new pump

  Donna Anderson Samson Properties

  104 Quigley Ct, Winchester, VA 22602
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  /2

  Not Listed For Sale

  • Studio
  • 1,693 Sq Ft

  408 Diehl St, Winchester, VA 22601

  408 Diehl St, Winchester, VA 22601
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  /50

  $574,900

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  1629 Pondview Dr, Winchester, VA 22601

  Discover tranquility and spacious living in this exceptional 4-bedroom, 3.5-bath home, with a main-level primary suite, ideally situated on one half of an acre backing to picturesque trees and wide-open fields. From the moment you step inside, you'll appreciate the meticulously maintained interior and inviting open floor plan. The living room features a cathedral ceiling and a cozy gas fireplace,

  Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

  1629 Pondview Dr, Winchester, VA 22601
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  /15

  $1,450 - $1,500 per month

  Woodstock Terrace

  2 Beds

  1016 Woodstock Ln, Winchester, VA 22601

  Fully furnished apartments! TV, Internet provided!

  1016 Woodstock Ln, Winchester, VA 22601
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  /57

  $480,000 Sold Jun 06, 2025

  • 2,532 Sq Ft
  • $190/SF
  • 17 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1992

  151 Morning Glory Dr, Winchester, VA 22602

  You'll love the convenience of living in the Apple Ridge neighborhood on the east side of Winchester with easy access to Route 7 & I-81. The open floor plan with kitchen, breakfast area & family room offers a great space for everyone to be together during meal prep, homework time, watching TV or just spending time together talking about the day's events. Highlights include the view of the

  Gina Chatham Century 21 Redwood Realty

  151 Morning Glory Dr, Winchester, VA 22602
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  /11

  Est $128,110 Not Listed For Sale

  1137 Tomahawk Trail, Winchester, VA 22602

  1137 Tomahawk Trail, Winchester, VA 22602
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  /31

  $625,000

  • 3 Beds
  • 3 Baths
  • 3,078 Sq Ft

  114 Harvest Ridge Dr, Winchester, VA 22601

  Here is your chance to make the Village at Harvest Ridge your relaxing abode with abundance of open interior space and an true HOA who keeps your lawn in tip top shape. Being 55+ active adult community definitely has its up side for sure, but this immaculate craftsman ranch style has a floor plan where the kitchen has a ton of cabinetry and granite counter tops and the island has the bar seating

  Dave Spence RE/MAX Roots

  114 Harvest Ridge Dr, Winchester, VA 22601
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  /6

  $2,700 per month

  • 4 Beds
  • 2.5 Baths
  • 1,940 Sq Ft
  • House for Rent

  2004 Taylor Grace Ct, Winchester, VA 22601

  Spacious single family house featuring 4 bedrooms, 2.5 bathrooms, full unfinished basement, deck, fenced backyard, and two attached car garage.

  Minh-Thieng Le Levi Clarke, LLC

  2004 Taylor Grace Ct, Winchester, VA 22601
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  /33

  $355,000 Sold Jun 06, 2025

  • 1,740 Sq Ft
  • $204/SF
  • 61 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2009

  125 Monticello Square, Winchester, VA 22602

  Price Reduction! Welcome to this beautifully maintained end-unit townhome, perfectly situated in a sought-after commuter-friendly location on the east side of Winchester! With 3 bedrooms, 2 full baths, and 2 half baths, this home offers an ideal blend of space, comfort, and convenience. Step inside to discover an inviting layout featuring a bright and airy living room, a modern kitchen with ample

  Robin Gebhardt CENTURY 21 New Millennium

  125 Monticello Square, Winchester, VA 22602
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  /30

  Not Listed For Sale

  301 Great Mountain Ln, Winchester, VA 22602

  301 Great Mountain Ln, Winchester, VA 22602
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  /40

  $749,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,342 Sq Ft

  200 Sweetbriar Ln, Winchester, VA 22603

  Welcome to your dream escape! This custom-built cabin on 7.02 acres in Winchester, VA offers the perfect blend of peace, privacy, and high-end living. Whether you're seeking a serene getaway or a functional farmette, this property has it all — with a mix of open pasture and woods, it’s ideal for animals, gardening, or simply soaking in nature.Step inside to find gleaming hardwood floors flowing

  Lori Hoffman Realty ONE Group Old Towne

  200 Sweetbriar Ln, Winchester, VA 22603
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  /20

  $1,600 - $2,600 per month

  Apartment for Rent

  Studio-2 Beds

  114 N Loudoun St, Winchester, VA 22601

  Brand new fully furnished extended stay apartments in the heart of Old Town Winchester Virginia including all utilities, washer /dyer, high speed internet, free nightly and weekend parking ( 5pm to 8 am), keyless entry, 10' ceilings, exposed brick interior partitions and optional weekly cleaning.. More information can be found at themerchantsuites

  114 N Loudoun St, Winchester, VA 22601
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  /40

  $283,000 Sold Jun 06, 2025

  • 1,276 Sq Ft
  • $222/SF
  • 246 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1920

  123 Pingley Ln, Winchester, VA 22602

  Discover this charming home featuring two spacious bedrooms and one bathroom, with over 1,200 square feet of comfortable living space. Recent renovations include countertops, new flooring, a refreshed shower, and upgraded 16-inch insulation for added energy efficiency. The unfinished basement provides ample storage options. Outdoors, you’ll appreciate the covered front porch and the privacy of a

  Marisa Varley ERA Oakcrest Realty, Inc.

  123 Pingley Ln, Winchester, VA 22602
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  /28

  Est $404,866 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,261 Sq Ft

  125 Cheshire Ct, Winchester, VA 22602

  125 Cheshire Ct, Winchester, VA 22602
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  /32

  $499,900

  • 4 Beds
  • 4 Baths
  • 1,627 Sq Ft

  201 Parkway St, Winchester, VA 22601

  Freshly Renovated Charmer in Winchester!Welcome to 201 Parkway Street, a freshly updated home in the heart of Winchester! Previously tenant-occupied, this property has been thoughtfully refreshed and is ready for new owners. Recent Updates Include:Fresh interior paint throughoutRenovated kitchen and bathUpdated fixtures and finishesClean, move-in ready conditionThis home offers the perfect blend

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
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  /31

  $1,599 per month

  • 2 Beds
  • 3 Baths
  • 1,148 Sq Ft
  • Townhouse for Rent

  1109 Franklin St Unit 1109, Winchester, VA 22601

  Ready to Move In now, Cute Town-home, Complete house hardwood floor with 2 huge bedroom and walking closet on upper floor and big living room with kitchen dining combo on main floor, CUL-DE-SAC close to I-81 exit 315 Rt.7 , walking distance from shopping ctr and downtown 1 mile, set up visit with agent. city water bill will be added minimum $100/month

  Ram Beladia First American Real Estate

  1109 Franklin St Unit 1109, Winchester, VA 22601
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  /37

  $275,000 Sold Jun 05, 2025

  • 1,152 Sq Ft
  • $239/SF
  • 24 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1983

  353 Shawnee Ave, Winchester, VA 22601

  INVESTORS SPECIAL Tucked away on a quiet cul-de-sac, this 3-bedroom, 1.5-bath colonial offers 1,152 sq ft of comfortable living space with a flat yard and rear deck—perfect for outdoor gatherings or quiet evenings at home. Just minutes from the charm and conveniences of Old Town Winchester, with easy access to dining, shopping, and commuter routes.A solid choice for investors seeking rental

  Barton Chasler Realty ONE Group Old Towne

  353 Shawnee Ave, Winchester, VA 22601
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  /4

  Est $890,867 Not Listed For Sale

  601 W Jubal Early Dr, Winchester, VA 22601

  601 W Jubal Early Dr, Winchester, VA 22601
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  /28

  $499,900 Open Sat 11AM - 1PM

  • 6 Beds
  • 3 Baths
  • 2,793 Sq Ft

  811 Berryville Ave, Winchester, VA 22601

  DO YOU HAVE A LARGE FAMILY AND NEED YOUR OWN SPACE. HERE IS A 6 BEDROOMS 3 BATHROOMS WITH 3 FULL KITCHENS. ALMOST 2800 SQ. FT FINISHED. OFF STREET PARKING FOR 6 CARS. SHED AND STILL ROOM TO RELAX OUTBACK.

  Richard Kozlowski Long & Foster Real Estate, Inc.

  811 Berryville Ave, Winchester, VA 22601
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  /12

  $2,000 per month

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  914 Cedar Creek Grade, Winchester, VA 22601

  Property Id: 1520637Brand New Remodeled - Rental ListingWelcome to your dream rental home! This stunning brand new dwelling offers luxury and comfort in every detail. Located in a serene neighborhood, this home is perfect for those seeking a blend of modern amenities and tranquility.Key Features:- Bedrooms: 2- Bathrooms: 2- Vaulted Ceilings: Yes-

  914 Cedar Creek Grade, Winchester, VA 22601
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  /66

  $700,000 Sold Jun 05, 2025

  • 4,692 Sq Ft
  • $149/SF
  • 0 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2005

  125 Killaney Ct, Winchester, VA 22602

  ***Sellers Accepted an offer. Open House is cancelled for May 3rd. ***Welcome to 125 Killaney Ct! This beautifully upgraded home offers over 4,700 sq ft of living space across three finished levels, including 7 bedrooms or 5 bedrooms with 2 generously sized flex rooms or guest suites in the fully finished walk-out basement. A main-level bedroom with ensuite bath provides added convenience and

  Vanessa Couture ERA Oakcrest Realty, Inc.

  125 Killaney Ct, Winchester, VA 22602
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  /6

  Est $206,366 Not Listed For Sale

  106 Mate Ct, Winchester, VA 22602

  106 Mate Ct, Winchester, VA 22602
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  /36

  $365,000

  • 2 Beds
  • 2.5 Baths
  • 1,238 Sq Ft

  1312 S Kent St, Winchester, VA 22601

  Welcome to this beautifully maintained townhouse featuring 2 spacious bedrooms and 2.5 baths. Enjoy the convenience of both driveway parking and additional parking lot spaces. The modern kitchen boasts quartz countertops, a stylish backsplash, electric cooking, bamboo flooring, a pantry, and a reverse osmosis water system—perfect for any home chef. Located in the heart of downtown Winchester,

  Sheila Pack RE/MAX Roots

  1312 S Kent St, Winchester, VA 22601
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  /14

  $1,800 per month

  • 1 Bed
  • 1 Bath
  • 826 Sq Ft
  • House for Rent

  122 N Loudoun St Unit 204, Winchester, VA 22601

  Enjoy this beautiful luxury flat located in the heart of Old Town Winchester. Floor to ceiling windows, gleaming hardwood floors and natural quartz counter tops will leave you asking for nothing. This contemporary design includes keyless entry, dish TV, reserved parking in Loudoun Street Autopark and free Wi-Fi. You can also enjoy the upscale appliance which include washer/dryer. Electric to be

  Dave Spence RE/MAX Roots

  122 N Loudoun St Unit 204, Winchester, VA 22601
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  /47

  $355,000 Sold Jun 05, 2025

  • 2,730 Sq Ft
  • $130/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  312 Bryarly Rd, Winchester, VA 22603

  1/2 Acre NO HOA!!! Discover the perfect blend of character and comfort in this older home brimming with charm. This inviting residence boasts 3 spacious bedrooms, currently featuring 2 on the main level. The primary bedroom is impressively large and has the potential to be converted back into 2 separate bedrooms, having 3 bedrooms on the main floor. Step into the large living room, perfect for

  Stacey Mullins ERA Oakcrest Realty, Inc.

  312 Bryarly Rd, Winchester, VA 22603
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  /12

  Not Listed For Sale

  • Studio
  • 2,376 Sq Ft

  1021 Franklin St, Winchester, VA 22601

  1021 Franklin St, Winchester, VA 22601
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  /50

  $470,000

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft

  350 Lanny Dr, Winchester, VA 22601

  This beautifully remodeled 3-bedroom, 2-bathroom all-brick rancher is perfectly situated in the heart of Winchester, providing easy access to schools, downtown, Winchester Medical Center, shopping, dining, entertainment, and parks. With its thoughtful remodel, this home blends timeless charm with modern updates. The eat-in kitchen boasts stainless steel appliances (2023), making it perfect for

  Sheila Pack RE/MAX Roots

  350 Lanny Dr, Winchester, VA 22601
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  /19

  $1,599 per month

  • 2 Beds
  • 2.5 Baths
  • 1,147 Sq Ft
  • Townhouse for Rent

  1109 Franklin St, Winchester, VA 22601

  Welcome to your new home in Winchester, VA! This charming 2-bedroom, 2.5-bath townhouse boasts 1,147 square feet of comfortable living space perfect for individuals or small families. Enjoy a spacious living area with new flooring that seamlessly flows into an open kitchen equipped with modern appliances. Abundant natural light fills the home, enhancing its inviting atmosphere.OFFERED AT

  1109 Franklin St, Winchester, VA 22601
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  /80

  $429,000 Sold Jun 05, 2025

  • 3,128 Sq Ft
  • $137/SF
  • 9 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1965

  2820 Baldwin St, Winchester, VA 22601

  CHARMING SPLIT FOYER HOME WITH 4 BEDROOMS AND 3 FULL BATHROOMS IN WINCHESTER!!!!!THIS WELL-MAINTAINED SPLIT FOYER HOME IN WINCHESTER OFFERS A FUNCTIONAL LAYOUT AND PLENTY OF SPACE. THE MAIN LEVEL FEATURES 3 BEDROOMS AND 2 FULL BATHROOMS, INCLUDING A SEPARATE LIVING ROOM AND DINING AREA, EACH OFFERING A CONFORTABLE SPACE FOR FAMILY TIME AND ENTERTAINING. THE KITCHEN IS READY FOR YOUR PERSONAL

  Carolina Mosquera Weichert, REALTORS

  2820 Baldwin St, Winchester, VA 22601
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  /62

  Est $714,163 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,422 Sq Ft

  231 Summerfield Dr, Winchester, VA 22602

  231 Summerfield Dr, Winchester, VA 22602
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  /59

  $469,900

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  1085 Greenwood Rd, Winchester, VA 22602

  MUST SEE!! Sellers have lived in this CHARMING meticulously well maintained 1968 brick ranch sitting on 1 ACRE for 27+ years!! 27 years’ of PURE LOVE and it shows. LOCATION, LOCATION! Rt 7, Rt 50, Interstate 81 & Costco only a 5 minute drive. Historic Downtown Winchester 10 mins. & Jim Barnett Park 5 mins!! Once a 3 Bed/1 Bath on a septic system is now a 2 Bedroom (one ensuite with jacuzzi tub)

  Caroline W. Barb, REALTOR Jim Barb Realty, Inc.

  1085 Greenwood Rd, Winchester, VA 22602
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  /24

  $2,400 per month

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • House for Rent

  317 S Kent St, Winchester, VA 22601

  For Rent: 317 S Kent St, Winchester, VA.Live in the heart of historic downtown Winchester! This spacious 4-bedroom, 1.5-bath home offers 1,800 square feet of charm and comfort, just a short walk from shops, restaurants, and Shenandoah University. With front and back porches, a flat private backyard, and plenty of room to spread out, its ideal for student roommates, faculty, or anyone seeking

  Sarah Abderrazzaq Realty ONE Group Old Towne

  317 S Kent St, Winchester, VA 22601
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  /77

  $425,000 Sold Jun 05, 2025

  • 1,956 Sq Ft
  • $217/SF
  • 27 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1949

  137 Waterloo Ct, Winchester, VA 22602

  So many appealing features on this unique property!!! The 1.23 acre lot is full of fruit trees, perennials, tons of flower beds and beautiful mature blooming trees! House Features: (a full list of improvements and the year completed in the "Documents")*1956 SQFT on 2 levels/// 4 bedrooms & 2 baths*Updated Kitchen*SS appliances BOSCH!!!! including a gas range, built in microwave, dishwasher and

  Erika De Azagra ERA Oakcrest Realty, Inc.

  137 Waterloo Ct, Winchester, VA 22602
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  /45

  Est $557,969 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,426 Sq Ft

  2040 Taylor Grace Ct, Winchester, VA 22601

  2040 Taylor Grace Ct, Winchester, VA 22601

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